What To Do On A Layover In Chicago

Chicago is a fascinating place, so if you find yourself in the city with time to spare—take advantage! A layover can go a long way here, and with Chicago’s speedy public transportation system, getting somewhere fast is incredibly doable. The city is easily accessible from both O’Hare and Midway airport—so there really are no excuses.

If you have three hours…

If you’re coming into the city from O’Hare airport, you might have to rush. The Blue Line CTA train is by far the simplest way to get into the city, as the station is in the airport. Take the train into “The Loop,” which is what the stops downtown are called. Hop off and make sure to run to a Chicago classic—maybe Giordano’s for some deep dish (but be sure to call ahead), or Stan’s Donuts for a sugary experience. With Midway airport, the CTA is also within the airport, making it pretty easy to get into town fast. Take the Orange Line to State and Lake and you’ll be within walking distance of some of Chicago’s best iconic landmarks such as The Chicago Theatre sign and, of course, Cloud Gate, better known as “the Bean.”

If you have five hours…

If you have seven hours…

Seven hours is enough time to really enjoy the museum scene in Chicago. Museum Campus is the first place to stop. Spanning 57 acres, Museum Campus sits along the banks of gorgeous Lake Michigan and is home to some of the most famous places in Chicago: The Shedd Aquarium, The Field Museum, the Adler Planetarium, and, of course, Soldier Field, home to the Chicago Bears. If art is more appealing—or if you just want to live out that scene from Ferris Bueller’s Day Off—then the Art Institute is also well within walking distance.

If you have 12 hours…

12 hours is enough time to tick off some of the city’s most iconic sights. First stop would have to be Navy Pier, where a trip up the Ferris wheel is by far the best way to see the city. Then on to Willis Tower where you can walk out above the crowds on the famous SkyDeck ledge. Sampling the local cuisine is also a must, so head to Firecakes for a quick bite or to the award-winning Frontera Grill for something more upmarket. Or perhaps you could just take some time to relax at Riverwalk. There are fantastic wineries and restaurants, as well as a number of wonderful spots to sit and people watch.

Since you are here, we would like to share our vision for the future of travel - and the direction Culture Trip is moving in.

Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.

Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Culture Trips, Rail Trips and Private Trips. Our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.

Culture Trips are deeply immersive 5 to 16 days itineraries, that combine authentic local experiences, exciting activities and 4-5* accommodation to look forward to at the end of each day. Our Rail Trips are our most planet-friendly itineraries that invite you to take the scenic route, relax whilst getting under the skin of a destination. Our Private Trips are fully tailored itineraries, curated by our Travel Experts specifically for you, your friends or your family.

We know that many of you worry about the environmental impact of travel and are looking for ways of expanding horizons in ways that do minimal harm - and may even bring benefits. We are committed to go as far as possible in curating our trips with care for the planet. That is why all of our trips are flightless in destination, fully carbon offset - and we have ambitious plans to be net zero in the very near future.